BRPI0719223B1 - processos químicos para preparar azoxistrobina utilizando ordens específicas de reagente e adição de catalisador - Google Patents

processos químicos para preparar azoxistrobina utilizando ordens específicas de reagente e adição de catalisador Download PDF

Info

Publication number: BRPI0719223B1
Authority: BR; Brazil
Prior art keywords: formula; mol; compound; cyanophenol; methyl
Prior art date: 2006-10-09

Application number

BRPI0719223A

Other languages

English (en)

Portuguese (pt)

Inventor

John Whitton Alan

Campbell Boyd Ewan

Beveridge Gillian

Hugh Vass Jack

Original Assignee

Syngenta Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-10-09

Filing date

2007-10-02

Publication date

2017-02-14

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=37454241&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=BRPI0719223(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2007-10-02 Application filed by Syngenta Ltd filed Critical Syngenta Ltd

2014-05-27 Publication of BRPI0719223A2 publication Critical patent/BRPI0719223A2/pt

2017-02-14 Publication of BRPI0719223B1 publication Critical patent/BRPI0719223B1/pt

Links

WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 title description 20
239000005730 Azoxystrobin Substances 0.000 title description 6
239000003054 catalyst Substances 0.000 title description 6
239000003153 chemical reaction reagent Substances 0.000 title description 4
238000001311 chemical methods and process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 100
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 93
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 claims description 92
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 90
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 56
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 37
229910000027 potassium carbonate Inorganic materials 0.000 claims description 23
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 22
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 22
229940011051 isopropyl acetate Drugs 0.000 claims description 22
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 20
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 18
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 13
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
WOADFQRFAAYIKX-UHFFFAOYSA-M potassium;2-cyanophenolate Chemical compound [K+].[O-]C1=CC=CC=C1C#N WOADFQRFAAYIKX-UHFFFAOYSA-M 0.000 claims description 5
239000003701 inert diluent Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
239000012973 diazabicyclooctane Substances 0.000 description 77
238000006243 chemical reaction Methods 0.000 description 61
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000000370 acceptor Substances 0.000 description 25
239000003085 diluting agent Substances 0.000 description 24
235000011181 potassium carbonates Nutrition 0.000 description 22
239000002904 solvent Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 17
239000002585 base Substances 0.000 description 14
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 13
YRYZZSRRDCTETP-DHZHZOJOSA-N methyl (e)-2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(Cl)=NC=N1 YRYZZSRRDCTETP-DHZHZOJOSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
239000012071 phase Substances 0.000 description 9
238000005292 vacuum distillation Methods 0.000 description 9
-1 2-cyanophenoxy Chemical group 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
239000002002 slurry Substances 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
235000019797 dipotassium phosphate Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
239000008096 xylene Substances 0.000 description 2
YDHPXCHZYXPZIS-VURMDHGXSA-N (3z)-3-(methoxymethylidene)-1-benzofuran-2-one Chemical compound C1=CC=C2C(=C/OC)/C(=O)OC2=C1 YDHPXCHZYXPZIS-VURMDHGXSA-N 0.000 description 1
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
IELHIACVIURUJP-JXMROGBWSA-N (e)-2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoic acid Chemical compound CO\C=C(\C(O)=O)C1=CC=CC=C1OC1=CC(Cl)=NC=N1 IELHIACVIURUJP-JXMROGBWSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
SUBFZYQWYBUTGO-UHFFFAOYSA-N 2-ethyl-n,n-di(propan-2-yl)butan-1-amine Chemical compound CCC(CC)CN(C(C)C)C(C)C SUBFZYQWYBUTGO-UHFFFAOYSA-N 0.000 description 1
YQVKRULJRQDXJA-UHFFFAOYSA-N 2-hydroxy-6-methylbenzonitrile Chemical compound CC1=CC=CC(O)=C1C#N YQVKRULJRQDXJA-UHFFFAOYSA-N 0.000 description 1
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229930182692 Strobilurin Natural products 0.000 description 1
XXMBNIBCSQZPRE-UHFFFAOYSA-N [Na].C(#N)C1=C(C=CC=C1)O Chemical compound [Na].C(#N)C1=C(C=CC=C1)O XXMBNIBCSQZPRE-UHFFFAOYSA-N 0.000 description 1
KSMDONYVDNGJLB-UHFFFAOYSA-N [Na].N12CCCCCC2=NCCC1.C(#N)C1=C(C=CC=C1)O Chemical group [Na].N12CCCCCC2=NCCC1.C(#N)C1=C(C=CC=C1)O KSMDONYVDNGJLB-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000007805 chemical reaction reactant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000006260 foam Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000002309 gasification Methods 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001463 metal phosphate Inorganic materials 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
BTTXESIFAHCXMK-UHFFFAOYSA-N methyl 2-methoxyprop-2-enoate Chemical compound COC(=C)C(=O)OC BTTXESIFAHCXMK-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
OXQMIXBVXHWDPX-UHFFFAOYSA-N n,n,2-trimethylpropan-2-amine Chemical compound CN(C)C(C)(C)C OXQMIXBVXHWDPX-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
MTEWAFVECQBILW-UHFFFAOYSA-N n-tert-butylcyclohexanamine Chemical compound CC(C)(C)NC1CCCCC1 MTEWAFVECQBILW-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

BRPI0719223A 2006-10-09 2007-10-02 processos químicos para preparar azoxistrobina utilizando ordens específicas de reagente e adição de catalisador BRPI0719223B1 (pt)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB0619941.8A GB0619941D0 (en)	2006-10-09	2006-10-09	Chemical process
GB0619941.8		2006-10-09
PCT/GB2007/003735 WO2008043978A1 (en)	2006-10-09	2007-10-02	Preparation of azoxystrobin

Publications (2)

Publication Number	Publication Date
BRPI0719223A2 BRPI0719223A2 (pt)	2014-05-27
BRPI0719223B1 true BRPI0719223B1 (pt)	2017-02-14

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BRPI0719223A BRPI0719223B1 (pt)	2006-10-09	2007-10-02	processos químicos para preparar azoxistrobina utilizando ordens específicas de reagente e adição de catalisador

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US (1)	US8552185B2 (pl)
EP (2)	EP2076498B1 (pl)
JP (1)	JP5275997B2 (pl)
KR (1)	KR101410801B1 (pl)
CN (1)	CN101522639A (pl)
AU (1)	AU2007306153B2 (pl)
BR (1)	BRPI0719223B1 (pl)
CA (1)	CA2665458C (pl)
ES (1)	ES2534897T3 (pl)
GB (1)	GB0619941D0 (pl)
MX (1)	MX2009003698A (pl)
MY (1)	MY147633A (pl)
NZ (1)	NZ575745A (pl)
PL (1)	PL2076498T3 (pl)
PT (1)	PT2076498E (pl)
RU (1)	RU2456277C2 (pl)
UA (1)	UA93424C2 (pl)
WO (1)	WO2008043978A1 (pl)
ZA (1)	ZA200902393B (pl)

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CN102516122B (zh) *	2011-11-08	2014-11-05	上海禾本药业有限公司	制备邻羟基苯甲腈的dmf溶液的方法
CN102399195A (zh) *	2011-12-08	2012-04-04	北京颖新泰康国际贸易有限公司	一种嘧菌酯中间体的合成方法
JP2015083541A (ja) *	2012-02-03	2015-04-30	アグロカネショウ株式会社	対称性４，６−ビス（アリールオキシ）ピリミジン化合物の製造方法
CN102690237A (zh) *	2012-06-11	2012-09-26	江西中科合臣实业有限公司	一种合成高纯度嘧菌酯的方法
CN103145627B (zh) *	2013-02-28	2015-10-07	河北威远生化农药有限公司	一种嘧菌酯的合成方法
CN103265496B (zh) *	2013-05-16	2015-02-25	北京颖泰嘉和生物科技有限公司	一种嘧菌酯的制备方法
TWI621614B (zh) *	2013-05-28	2018-04-21	科麥農股份有限公司	4,6-雙(芳氧基)嘧啶衍生物的製備方法
CN104672146A (zh) *	2013-11-26	2015-06-03	上海泰禾化工有限公司	一种新的高产率制备嘧菌酯的方法
CN104119282B (zh) *	2014-08-05	2016-06-29	江苏七洲绿色化工股份有限公司	一种嘧菌酯的脱色和提纯方法
CN104230820B (zh) *	2014-09-16	2016-09-28	重庆紫光国际化工有限责任公司	嘧菌酯的合成方法
CN104230819B (zh) *	2014-09-16	2017-05-03	重庆紫光国际化工有限责任公司	嘧菌酯的合成方法
CN104311493B (zh) *	2014-09-16	2016-08-24	重庆紫光国际化工有限责任公司	嘧菌酯的合成方法
CN104230821B (zh) *	2014-09-16	2016-07-06	重庆紫光国际化工有限责任公司	嘧菌酯的合成方法
CN105536873B (zh) *	2016-02-05	2017-11-28	帕潘纳(北京)科技有限公司	一种复合催化剂及其应用
CN109384728A (zh) *	2017-08-07	2019-02-26	华东理工大学	嘧菌酯通道型溶剂化物及其制备方法
CN109721548B (zh) *	2017-10-31	2020-11-13	南通泰禾化工股份有限公司	一种嘧菌酯的制备方法
CN113825744A (zh)	2019-04-18	2021-12-21	Upl有限公司	用于制备杀真菌活性嗜球果伞素化合物及其中间体的方法
BR112021020906A2 (pt)	2019-04-18	2022-04-19	Upl Ltd	Processo para a preparação de azoxistrobina e intermediários da mesma
KR102683529B1 (ko)	2019-08-23	2024-07-09	주식회사 엘지화학	아족시스트로빈의 제조방법
CN114685376B (zh) *	2020-12-28	2024-06-07	北京颖泰嘉和生物科技股份有限公司	嘧菌酯中间体的制备方法
CN114685377B (zh) *	2020-12-31	2024-05-31	北京颖泰嘉和生物科技股份有限公司	嘧菌酯类化合物的制备方法
CN114957134B (zh)	2022-05-26	2024-07-16	安徽广信农化股份有限公司	一种制备嘧菌酯及其中间体的方法
CN115043781A (zh) *	2022-07-28	2022-09-13	内蒙古佳瑞米精细化工有限公司	一种嘧菌酯产品的合成方法
WO2026078205A1 (en)	2024-10-10	2026-04-16	Syngenta Crop Protection Ag	Process for the preparation of intermediates for the preparation of azoxystrobin

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GB0114408D0 (en) *	2001-06-13	2001-08-08	Syngenta Ltd	Chemical process
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GB0508422D0 (en) *	2005-04-26	2005-06-01	Syngenta Ltd	Chemical process

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- 2007-10-02 AU AU2007306153A patent/AU2007306153B2/en active Active
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- 2007-10-02 CN CNA2007800375956A patent/CN101522639A/zh active Pending
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Also Published As

Publication number	Publication date
UA93424C2 (en)	2011-02-10
RU2456277C2 (ru)	2012-07-20
AU2007306153B2 (en)	2012-07-05
AU2007306153A1 (en)	2008-04-17
JP5275997B2 (ja)	2013-08-28
ZA200902393B (en)	2010-03-31
CN101522639A (zh)	2009-09-02
ES2534897T3 (es)	2015-04-30
BRPI0719223A2 (pt)	2014-05-27
KR20090060336A (ko)	2009-06-11
CA2665458A1 (en)	2008-04-17
JP2010505805A (ja)	2010-02-25
US8552185B2 (en)	2013-10-08
EP2076498A1 (en)	2009-07-08
CA2665458C (en)	2014-03-25
EP2712864A1 (en)	2014-04-02
MY147633A (en)	2012-12-31
US20100036124A1 (en)	2010-02-11
RU2009117654A (ru)	2010-11-20
MX2009003698A (es)	2009-04-22
EP2076498B1 (en)	2015-02-25
GB0619941D0 (en)	2006-11-15
PL2076498T3 (pl)	2015-07-31
KR101410801B1 (ko)	2014-06-23
WO2008043978A1 (en)	2008-04-17
PT2076498E (pt)	2015-05-11
NZ575745A (en)	2010-11-26

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Date	Code	Title	Description
2016-08-30	B06A	Notification to applicant to reply to the report for non-patentability or inadequacy of the application [chapter 6.1 patent gazette]
2016-12-13	B09A	Decision: intention to grant [chapter 9.1 patent gazette]
2017-02-14	B16A	Patent or certificate of addition of invention granted
2018-06-26	B25G	Requested change of headquarter approved
2018-07-17	B22O	Other matters related to patents and certificates of addition of invention: legal action concerning patent
2020-04-22	B19A	Notification of judicial decision: notification of judicial decision	Free format text: INPI NO 52400.121199/2018-37 PROCESSO JUDICIAL : 5005880-83.2018.4.02.5101 NUP: 00408.044797/2018-10 PARTE AUTORA: UPL DO BRASIL INDUSTRIA E COMERCIO DE INSUMOS AGROPECUARIOS S.A. PARTE RE: SYNGENTA LIMITED (GB) E INPI-INSTITUTO NACIONAL DE PROPRIEDADE INDUSTRIAL DECISAO: TRANSITO EM JULGADO DA SENTENCA QUE HOMOLOGOU A DESISTENCIA DA ACAO, JULGANDO O PROCESSO EXTINTO SEM APRECIACAO DO MERITO, DEVE TAL DECISAO SER PUBLICADA NA RPI, RETIRANDO-SE O STATUS DE SUB JUDICE DAS PATENTES IMPUGNADAS, PI 0610381-2 E PI 0719223-1.

Publication	Publication Date	Title
BRPI0719223B1 (pt)	2017-02-14	processos químicos para preparar azoxistrobina utilizando ordens específicas de reagente e adição de catalisador
BRPI0610381A2 (pt)	2012-10-23	processo para preparar um composto, composto, e, composição
BR122019022815B1 (pt)	2022-02-01	Processo para preparar azoxistrobina e seu derivado dimetóxi acetal
ES2384368T3 (es)	2012-07-04	Proceso de preparación de derivados del ácido 1-(2-halobifenil-4-il)-ciclopropanocarboxílico
PT1417180E (pt)	2007-03-30	Preparação de compostos de aminopirimidina
ES2675892T3 (es)	2018-07-13	Procedimiento de preparación de derivados de 4,6-bis (ariloxi) pirimidina
AU2014317729A1 (en)	2015-10-01	Methods for preparing azoxystrobin and intermediate thereof
US8183408B2 (en)	2012-05-22	Process for production of N-carbamoyl-tert-leucine
Brindisi et al.	2013	A stereoselective route to 6-substituted pyrrolo-1, 5-benzoxazepinones and their analogues
ES2369113T3 (es)	2011-11-25	Procedimiento mejorado para producir moxonidina.
JPWO2006083012A1 (ja)	2008-06-26	ピリミジン化合物の製造方法
WO2013115381A1 (ja)	2013-08-08	対称性４，６－ビス（アリールオキシ）ピリミジン化合物の製造方法
ES2848200T3 (es)	2021-08-05	Procedimiento para la preparación de 2-vinilfenilsulfonatos 3-sustituidos
HK1135097A (en)	2010-05-28	Preparation of azoxystrobin
KR20150050190A (ko)	2015-05-08	로수바스타틴 중간체인 (E)-t-부틸 2-(6-(2-(4-(4-플루오로페닐)-6-이소프로필-2-(N-메틸,메틸설폰아미도)피리미딘-5-일)비닐)-2,2-디메틸-1,3-디옥산-4-일)아세테이트의 제조 방법